[2,3-bis(hexadecanoyloxy)propoxy]({2-[(E)-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene]amino]ethoxy})phosphinic acid

• ChemBase ID: 175744
• Molecular Formular: C57H100NO8P
• Molecular Mass: 958.379561
• Monoisotopic Mass: 957.7186558
• SMILES: C(=N\CCOP(=O)(O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC(COP(=O)(OCC/N=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)O)COC(=O)CCCCCCCCCCCCCCC
• InChI: InChI=1S/C57H100NO8P/c1-8-10-12-14-16-18-20-22-24-26-28-30-32-39-55(59)63-48-53(66-56(60)40-33-31-29-27-25-23-21-19-17-15-13-11-9-2)49-65-67(61,62)64-47-46-58-45-43-51(4)37-34-36-50(3)41-42-54-52(5)38-35-44-57(54,6)7/h34,36-37,41-43,45,53H,8-33,35,38-40,44,46-49H2,1-7H3,(H,61,62)/b37-34+,42-41+,50-36+,51-43+,58-45+
• InChIKey: KWYWUBDCIVMKAT-GXYBYMFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2,3-bis(hexadecanoyloxy)propoxy]({2-[(E)-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene]amino]ethoxy})phosphinic acid
• IUPAC Traditional name: 2,3-bis(hexadecanoyloxy)propoxy(2-[(E)-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene]amino]ethoxy)phosphinic acid
• Synonyms: (all-E)-1,2-di-2-Palmitin [[3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenylidene]amino]ethyl hydrogen phosphate; DP-NRPE; NRPE

Database IDs

• CAS Number: 30576-47-7
• PubChem SID: 164231654
• PubChem CID: 71751265

CALCULATED PROPERTIES

• Acid pKa: 1.8049856
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 15.758235
• LogD (pH = 7.4): 15.152477
• Log P: 15.782735
• Molar Refractivity: 284.9043 cm^3
• Polarizability: 111.13677 Å^3
• Polar Surface Area: 120.72 Å^2
• Rotatable Bonds: 45
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N900100

A pigment that forms during the visual cycle in vertebrates leading to harmful byproducts of this biosynthetic pathway.

REFERENCES

• Anderson, R., et al.: Biochem., 9, 3624 (1970)
• Liu, J., et al.: J. Biol Chem., 38, 29354 (2000)